Sodium hydride → HCID 10592900, compound

HRID 393169Notes

Reaction equation

HRID 393169 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH:14]=[CH:13][CH:12]=[CH:11]1.Br[CH:16]([C:22]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=1)[C:17]([O:19][CH2:20][CH3:21])=[O:18]>C1COCC1>[CH2:20]([O:19][C:17](=[O:18])[CH:16]([C:22]1[CH:23]=[CH:24][C:25]([CH3:28])=[CH:26][CH:27]=1)[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH:14]=[CH:13][CH:12]=[CH:11]1)[CH3:21]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 7123342-(1H-Pyrrol-1-Yl)PhenolHCID 13608722HCID 13608722, compound

Product 1

HCID 10592900HCID 10592900, compoundYield 54.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium hydride (90 mg, 3.9 mmol) was added to a solution of 1-(2-hydroxyphenyl)pyrrole (0.41 g, 2.5 mmol) in anhydrous THF (5 mL) at RT. The reaction mixture was stirred for 1 h at RT, and then a solution of ethyl α-bromo-p-tolylacetate (1.0 g, 3.9 mmol) in anhydrous THF (5 mL) was added dropwise. After 12 h at RT, the solvent was removed in vacuo, and the residue was taken up in dichloromethane. The organic layers were washed with brine, dried, and evaporated. The residue was purified by chromatography (toluene) to give 0.46 g of the title compound as a colorless oil; IR (neat): 1734 cm−1; 1H NMR(CDCl3) d 1.16 (t, 3 H, J=7.0 Hz), 2.33 (s, 3 H), 4.13 (q, 2 H, J=7.0 Hz), 5.48 (s, 1H), 6.31 (m, 2 H), 6.95-7.40 (m, 10 H).

Workup

  1. waitAfter 12 h at RT
  2. customthe solvent was removed in vacuo
  3. washThe organic layers were washed with brine
  4. customdried
  5. customevaporated
  6. customThe residue was purified by chromatography (toluene)

Sources & evidence

ORD record
ord-bfd4c08752d84ae98ddbca7d3cb91f42
Source dataset
uspto-grants-2004_10
Patent number
US06806267B1

Reaction notes

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